Key West Vacation Guide

Key West is a VERY dog-friendly town! Furry friends are even allowed in some bars and restaurants on our island. There are also several dog parks and even a dog beach! If you wish to travel with your dog(s), we do have dog-friendly vacation homes available.

john truman bedroom

Key West Retreats At Truman Suites

Fall is the perfect time to experience Key West retreats at Truman Suites. The Truman Suites offers five separate fully equipped suites just a few steps from famous Duval Street. The two-story complex offers 7 bedrooms, 5 bathrooms and sleeps up to 18. The Truman...Read more
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Key West Vacation Guide
key west palms at sunset

Key West Monthly Vacation Home Spotlight

Our Key West weather is absolutely perfect from October through January making it the ideal getaway destination for extended vacations. Warm enough to lounge by the pool, snorkel our reefs and to kayak along the mangroves. Visiting couples, seniors and families will find it the...Read more
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Key West Vacation Guide
island days pool

8 Caribbean Homes For The Holidays

Historic Key West Vacation Rentals has the premier collection of boutique luxury homes and we're happy to present to you these eight Caribbean homes for the holidays! You've spent most of the year quarantined and landlocked while dreaming of an exotic, tropical getaway. Key West...Read more
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Key West Vacation Guide
al fresco dining at Inn Cogneato in Key West

Boutique Key West Rental Spotlight

Inn Cogneato is a newly renovated beautiful 2 bedroom 2 bath home located in one of the oldest parts of Historic Key West. We so excited to share the updates with you this luxury boutique rental comes with a very special tropical rate for November...Read more
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Key West Vacation Guide
southard comfort pool

Luxury NYE Key West Vacation Rentals

Chances are you're ready to turn the page and to say goodbye to 2020. We couldn't agree more and we also can't think of a better time to wrap this one up, put a bow on it, load it into a fireworks cannon and blast...Read more
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Key West Vacation Guide
Petronia Christmas Table

A Socially Distant Key West Christmas

Have yourself a socially distant Key West Christmas and for this moment in time, your troubles will be far away. Historic Key West Vacation Rentals invites you to experience our collection of boutique luxury vacation homes with plenty of yuletides for days. Faithful friends who...Read more
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Key West Vacation Guide
thanksgiving feast

Luxury Key West Thanksgiving Rentals

The centerpiece of Thanksgiving is always a large meal centered around a large turkey with lots of side dishes and desserts and traditions that celebrate family and friends and culture. This is a year when coming together for mashed potatoes, stuffing, cranberry sauce, hugs and...Read more
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Key West Vacation Guide
a Christmas wreath at Lemonade Mermaid Vacation Rentals in Key West.

Key West Boutique Rental Spotlight

Key West is known for its community spirit where all are welcome to join in joyous celebrations of Thanksgiving, Christmas and New Year's. These are the times we decorate for the season and regale locals and visitors alike with art, fine food and holiday libations...Read more
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Key West Vacation Guide
little miss magic den

7 Amenities To Add To Your Key West Experience

2020 is not the year to be hoarding your vacation days. We all need time away from work and routines and that's especially important when we're spending much more time in our homes. You may be able to roll over some of your vacation days,...Read more
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Key West Vacation Guide
waterfall feature at southard comfort vacation rentals

Work Remote from Key West

If you're currently balancing virtual school for your children and meeting deadlines while working from home, it's time for a change of scenery. Trade in the drudgery for creativity and outdoor activities that translate into learning, plant life, moon phases, star gazing, and assorted natural...Read more
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Key West Vacation Guide

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